Conjugated molecule with star d-a structure based on triindeno five-membered aromatic heterocycle and its preparation method and application
A technology of conjugated molecules and aromatic heterocycles, applied in the field of star-shaped D-A structure conjugated molecules and their preparation, can solve the problems of poor absorption, poor batch repeatability, difficult purification, etc., and achieve high carrier mobility, high Effects of energy conversion efficiency, effective charge transport
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[0053] The present invention also provides a preparation method of a star-shaped D-A structure conjugated molecule based on a triindeno five-membered aromatic heterocycle, which specifically includes the following steps:
[0054] Step 1, benzene triboronate and 2-bromo-3 carboxylate five-membered aromatic heterocyclic compound with a molar ratio of 1:3 to 15 are mixed with water with a volume ratio of 1:1 to 3 under palladium catalysis Cross-coupling reaction is carried out in a mixed solvent system with toluene, and the obtained compound undergoes an addition reaction with an active metal reagent, and the desired compound with R is obtained through a ring-closing reaction. 1 The three-indeno five-membered aromatic heterocyclic ring center core of the base; the 2-bromo-3 formic acid ester five-membered aromatic heterocyclic compound is 2-bromo-3-formic acid methyl thiophene, 2-bromo-3-formic acid ethyl Esterthiophene, 2-bromo-3-carboxylate methylfuran, 2-bromo-3-carboxylate et...
Embodiment 1
[0068] A star-shaped D-A structure conjugated molecule based on a three-indeno five-membered aromatic heterocycle with the structure of BTCT-3IC, the synthesis route is as follows:
[0069]
[0070] (1) Synthesis of an intermediate whose chemical structure is a: under argon protection, (22.7g, 102.6mmol) methyl 2-bromothiophene-3-carboxylate, (12.0g, 26.3mmol) 1,3,5 - Benzenetriboronic acid tripinacol ester and (3.0g, 2.63mmol) tetrakis (triphenylphosphine) palladium add in 500mL two-necked flask, then add 200mL deoxygenated toluene and 100mL deoxygenated 2M potassium carbonate aqueous solution, stir and Heated to 85°C for 48h. Stop the reaction, extract with ether, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, spin dry after filtration, and separate by column chromatography, the eluent is petroleum ether / ethyl acetate (volume ratio 5:1), and a white solid is obtained Product 10.0g, yield 76%. 1 H NMR (400MHz, CDCl 3 ) δ 7.66 (...
Embodiment 2
[0075] A star-shaped D-A structure conjugated molecule based on a three-indeno five-membered aromatic heterocycle with the structure of BTCT-3TIC, the synthesis route is as follows:
[0076]
[0077] Wherein, the synthesis of intermediate a and b is the same as in Example 1.
[0078] (1) Synthesis of intermediates with chemical structure d: under the protection of argon, add (0.2g, 0.15mmol) intermediate b and 25mL tetrahydrofuran into a 100mL three-necked flask, cool to -78°C, and slowly add 2.5M n-butyl Lithium base 0.36mL, keep the temperature for 1h after the dropwise addition. Then, trimethyltin chloride (0.22 g, 0.11 mmol) was added, slowly returned to room temperature, and the reaction was stirred overnight. After the reaction was completed, KF aqueous solution was added and stirred for 1 h, extracted with ether, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and spin-dried, and the solid was washed with methanol to obtain 0.21 g of a sol...
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